O-Methylhydroxylamine hydrochloride → HCID 53895774, compound

HRID 399278Notes

Reaction equation

HRID 399278 reaction equation
CC(C)([O-])C.[K+].Cl.[O:8]([NH2:10])[CH3:9].[C:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([N:28]3[C:36]4[C:31](=[CH:32][C:33]([O:43][CH3:44])=[C:34]([O:37][CH2:38][CH2:39][N:40]([CH3:42])[CH3:41])[CH:35]=4)[CH:30]=[CH:29]3)=[O:27])=[CH:22][CH:21]=2)=[C:16]([CH3:45])[CH:15]=1)(=O)[CH3:12]>CO>[CH3:42][N:40]([CH3:41])[CH2:39][CH2:38][O:37][C:34]1[CH:35]=[C:36]2[C:31]([CH:30]=[CH:29][N:28]2[C:26]([C:23]2[CH:22]=[CH:21][C:20]([C:17]3[CH:18]=[CH:19][C:14]([C:11](=[N:10][O:8][CH3:9])[CH3:12])=[CH:15][C:16]=3[CH3:45])=[CH:25][CH:24]=2)=[O:27])=[CH:32][C:33]=1[O:43][CH3:44]

Participants

5

Reactant 3

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 18970491HCID 18970491, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 53895774HCID 53895774, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Potassium t-butoxide (0.11 g, 1.0 mmole) was added to methanol (10 ml) with stirring under argon and after 20 minutes at room temp. the solution was treated with methoxylamine hydrochloride (0.11 g, 1.3 mmole). The resulting mixture was stirred at room temp. for 20 minutes, then treated with a solution of 1-(4'-acetyl-2'-methylbiphenyl-4-carbonyl)-6-(2-dimethylaminoethoxy)-5-methoxy-1H-indole (E5, 0.30 g, 0.63 mmole) in methanol (10 ml). The mixture was stirred for 18 h at room temp. followed by heating under reflux for 3 h, then concentrated in vacuo. The residue was treated with 10% Na2 CO3 solution and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to leave a yellow oil, which was chromatographed on silica gel eluting with 0-5% methanol/dichloromethane to afford the title compound (0.20 g, 63%), mp 120°-121° C.

Workup

  1. stirringThe resulting mixture was stirred at room temp. for 20 minutes
  2. stirringThe mixture was stirred for 18 h at room temp.
  3. temperatureby heating
  4. temperatureunder reflux for 3 h
  5. concentrationconcentrated in vacuo
  6. additionThe residue was treated with 10% Na2 CO3 solution
  7. extractionextracted with ethyl acetate
  8. dry with materialThe extract was dried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customto leave a yellow oil, which
  11. customwas chromatographed on silica gel eluting with 0-5% methanol/dichloromethane

Sources & evidence

ORD record
ord-ee9575af8f6645228fdf34921bbe3c72
Source dataset
uspto-grants-1998_10
Patent number
US05817833

Reaction notes

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